When the Cubs went ahead and signed Alex Bregman for $175 million, Red Sox fans were left asking why Boston didn’t make the first move. Reports later suggested the Red Sox simply couldn’t match the Cubs’ offer, but that explanation only raised more questions about the team’s overall plan.

After already missing out on Pete Alonso and having to settle for Willson Contreras, losing Bregman felt like the final straw for many fans, sparking a full-blown uproar. Now, Red Sox president Craig Breslow has spoken out about what went wrong in the Bregman pursuit, and his comments may only add more fuel to the fire.

“Once you extend the aging curve past 31, you’re really just reallocating dollars from surplus value into negative WAR insurance. The extra $10 million, combined with opt-out leverage, meaningfully compresses our long-term optionality and tax efficiency. We felt five for $165 million, fully guaranteed, was the rational equilibrium. We’re very comfortable being disciplined there,” MLB insider Jim Dalfino quoted Breslow.

Well, the Red Sox have built a reputation over the years for being careful with long-term deals for players over 30. More often than not, the front office leans toward shorter contracts and flexibility, choosing financial restraint over going all in on aging stars. This time was no different, as Breslow made it clear that the team stuck to that long-standing philosophy instead of getting aggressive for Alex Bregman.

What really caught fans off guard, though, was that Boston reportedly offered as much as $165 million for Bregman. That’s just $10 million shy of what the Cubs ultimately offered, which naturally led to the big question: couldn’t the Red Sox have found that extra $10 million? For many fans, that small gap made the decision even harder to swallow.

If you look closely at Breslow’s comments, they line up perfectly with how the Red Sox have been operating in recent years.

The front office has shown little interest in handing out lengthy contracts to older players, instead pouring resources into the farm system. The organization is betting big on prospects like Roman Anthony, Kristian Campbell, and Marcelo Mayer to grow into everyday contributors. Ownership, led by John Henry, has been consistent in its smart spending.

They don’t want to mortgage the future for the present by committing to massive deals they might regret later. However, after losing out on Bregman, it’s clear the fans aren’t exactly on the same page with that approach.

Fans are giving up on the Red Sox

What does it mean if the Red Sox continue to lose marquee players in the name of smart spending? Fans wonder. “Being very disciplined, but soon you will have no stars. Teams without stars rarely win. We got Crochet and Anthony,” one fan said. “He talks like an AI bot. Please help us,” added another.

If we look at how the Red Sox front office responded after missing out on Pete Alonso, Edwin Díaz, and now Alex Bregman, a common template is evident. The team insists it has its own plan. However, according to fans, if the team keeps missing out on star free agents, what is the point of playing it smart? Take any player who hits free agency after a strong season, and a significant amount usually needs to be spent.

If the Red Sox continue to shy away from investment, remaining free agents like Bo Bichette and Kyle Tucker might not even be on their radar. “OK, so what will he say about Bo?” another user wondered.

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Not signing Bregman for just an extra $10 million has also left fans stunned. “Imagine a $14 billion sports conglomerate complaining about $10 million. Pathetic,” one user added. “Yep, I’m sure $10M, when the luxury tax will be $300M by then, will really hamstring them. What a joke.”

For those unfamiliar, the Red Sox owners are the same group that also manages Liverpool FC. So, if a $14 billion conglomerate shies away from spending an extra $10 million, fans are understandably stunned.

Nevertheless, there are still a few marquee players available in free agency. Let’s see if any of them end up in Boston.